Hydroxide → Ethyl trifluoroacetate

HRID 1838023Notes

Reaction equation

ClC1C=CC2NC(=O)[O:8][C@:7](C#CC3CC3)([C:12]([F:15])([F:14])[F:13])C=2C=1.Cl[C:23]1[CH:29]=CC(N)=CC=1.C(Cl)(=[O:35])C(C)(C)C.[OH-]>>[F:13][C:12]([F:15])([F:14])[C:7]([O:35][CH2:29][CH3:23])=[O:8]

Participants

Reactant 4

HCID 961Hydroxide

HCID 78124-Chloroaniline

HCID 62493Pivaloyl chloride

HCID 64139Efavirenz

Product 1

HCID 9794Ethyl trifluoroacetate

Procedure

Synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one can be accomplished through the use of commercially available 4-chloroaniline. After reaction with pivaloyl chloride in the presence of hydroxide to afford the corresponding amide, treatment with an alkyl lithium and ethyl triflouroacetate is followed by acidification with a mineral acid to provide the salt of the triflouroketone (Scheme 1).

Sources & evidence

ORD record: ord-c644e0e02d40468db940c83c0b4cd345
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673372B1

Reaction notes

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